1. bookVolume 12 (2013): Issue 2 (December 2013)
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SYNTHESIS AND REACTIONS OF NEW DERIVATIVES OF FURO[3,2-b]PYRROLE

Published Online: 31 Dec 2013
Page range: 100 - 107
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28 Jun 2012
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© 2020 Sciendo

Synthesis of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate is taken place in two step synthesis. Vilsmeier-Haack reaction of 4H-furo[3,2-b]pyrrole-5-carboxylate 1 led to methyl 2-formyl-4H-furo[3,2- b]pyrrole-5-carboxylate 4, which served as starting compound for synthesis of furo[3,2-b]pyrrole-2- aldoxime 5 and methyl 2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-4H-furo[3,2-b]pyrrole-5- carboxylate 7. The hydrazinolysis of 1 was prepared by carbohydrazide 2, which subsequently reacted with aldehydes to form of derivatives 3. Pyrazole derivatives 11 were prepared by the reaction of azlactone 9 with derivatives 10. Reactions were carried out under microwave irradiation or at classical heating.

Keywords

GAJDOŠ, P., PAVLÍKOVÁ, S., BUREŠ, F., KRUTOŠÍKOVÁ, A.: 2-[3- (Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: Synthesis and reactions. Cent. Eur. J.Chem., 3, 2005, 311-325.Search in Google Scholar

GAŠPAROVÁ, R., MONCMAN, M., HORVÁTH, B.: Microwave assisted reactions of 2-[3-(trifluoromethyl)phenyl]-4-R1-furo[3,2-b]pyrrole-5-carboxhydrazides.Cent. Eur. J. Chem., 6, 2007, 180-187.Search in Google Scholar

GAŠPAROVÁ, R., ZBOJEK, D., LÁCOVÁ, M., KRÁĽOVÁ, K., GATIAL, A., HORVÁTH, B., KRUTOŠÍKOVÁ, A.: Reactions of substituted furo[3,2- b]pyrrole-5-carboxhydrazides and their biological activity. Cent. Eur. J. Chem., 3(4), 2005, 622-646.Search in Google Scholar

GORUGANTULA, P. S., MARTÍNEZ-CARRERO, M. G., DANTALE, W. S., SÖDERBERG, C. G. B.: Palladium-catalyzed reductive N-heterocyclization of alkenyl-substituted nitroarenes as a viable method for the preparation of bicyclic pyrrolofused heteroaromatic compounds. Tetrahedron, 66, 2010, 1800-1805.Search in Google Scholar

JORDÃO, K.A., SATHLER, C. P., FERREIRA, F.V., CAMPOS, R. V., DE SOUZA, C.B.V.M., CASTRO, C.H., LANNES, A., LOURENCO, A., RODRIGUES, R. C., BELLO, L. M., LOURENCO, C.S.M., CALVALHO, S.L.G., ALMEIDA, C.B.M, CUNHA, C.A.: Synthesis, antitubercular activity, and SAR study of N-substitutedphenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides. Bioorg. Med. Chem., 19, 2011, 5605-5611.Search in Google Scholar

KRUTOŠÍKOVÁ, A., DANDÁROVÁ, M., ALFÖLDI, J.: Synthesis and reactions of furo[3,2-b]pyrrole type aldehydes. Coll. Czech. Chem. Commun., 58, 1993, 2139-2149.Search in Google Scholar

KRUTOŠÍKOVÁ, A., DANDÁROVÁ, M., ALFÖLDI, J.: Substituted vinyl azides in the synthesis of condensed nitrogen heterocycles. Chem. Papers, 48, 1994, 268-273.Search in Google Scholar

PIECZONKA, M. A., STRZELCZYK, A., SADOWSKA, B., MLOSTOŃ, G., STACZEK, P.: Synthesis and evaluation of antimicrobial activity of hydrazones derived from 3-oxido-1H-imidazole-4-carbohydrazides. Eur. J. Med. Chem., 64, 2013, 389-395.Search in Google Scholar

PUTEROVÁ, Z., STERK, H., KRUTOŠÍKOVÁ, A.: Reaction of substituted furan-2- carboxaldehydes and furo[b]pyrrole type aldehydes with hippuric acid. Molecules, 9, 2004, 11-21.Search in Google Scholar

TELVEKAR, N. V., BELUBBI, A., BAIRWA, K.V., SATARDEKAR. K.: Novel N′- benzylidene benzofuran-3-carbohydrazide derivatives as antitubercular and antifungal agents. Bioorg. Med. Chem. Lett., 22, 2012, 2343-2346.Search in Google Scholar

ULLOORA, S., SHABARAYA, R., RANGANATHAN, R., ADHIKARI, V.A.: Synthesis, anticonvulsant and anti-inflammatory studies of new 1,4- dihydropyridin-4-yl-phenoxyacetohydrazones. Eur. J. Med. Chem., 70, 2013, 341-349. Search in Google Scholar

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